Heterocyclic compound and organic light-emitting device including the same

ABSTRACT

Provided are a heterocyclic compound represented by Formula 1 and an organic light-emitting device including the same. The organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one heterocyclic compound represented by Formula 1.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of application Ser. No.16/800,484, filed on Feb. 25, 2020, which claim priority to and thebenefit of Korean Patent Application No. 10-2019-0021948, filed on Feb.25, 2019, in the Korean Intellectual Property Office, the entire contentof which is incorporated herein by reference.

BACKGROUND 1. Field

One or more embodiments relate to a heterocyclic compound and an organiclight-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices that producefull-color images, and also have wide viewing angles, high contrastratios, short response times, and excellent characteristics in terms ofbrightness, driving voltage, and response speed, as compared to otherdevices in the art.

The organic light-emitting device may include a first electrode on asubstrate, and a hole transport region, an emission layer, an electrontransport region, and a second electrode, which are sequentially on thefirst electrode. Holes provided from the first electrode may move towardthe emission layer through the hole transport region, and electronsprovided from the second electrode may move toward the emission layerthrough the electron transport region. Carriers, such as holes andelectrons, recombine in the emission layer to produce excitons. Theseexcitons transit (e.g., transition or relax) from an excited state to aground state, thereby generating light.

SUMMARY

Aspects of embodiments of the present disclosure provide a heterocycliccompound and an organic light-emitting device including the same.

Additional aspects of embodiments will be set forth in part in thedescription which follows and, in part, will be apparent from thedescription, or may be learned by practice of the presented embodiments.

An aspect of embodiments of the present disclosure provides aheterocyclic compound represented by Formula 1:

In Formula 1,

Y₁ may be N or P,

Y₂ may be B(R₁), P(═O)(R₁), or P(═S)(R₁),

X₁ and X₂ may each independently be O, S, N(R₂), C(R₂)(R₃), orSi(R₂)(R₃),

m1 and m2 may each independently be 0, 1, or 2, where m1+m2>0,

A₁ to A₃ may each independently be a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀ heterocyclicgroup,

a10, a20, and a30 may each independently be selected from 0, 1, 2, 3, 4,5, 6, 7, and 8,

R₁ to R₃, R₁₀, R₂₀, and R₃₀ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —C(═O)(Q₁),—N(Q₁)(Q₂), —P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁)(Q₂),

R₁ to R₃, R₁₀, R₂₀, and R₃₀ may optionally be linked to form asubstituted or unsubstituted C₅-C₆₀ carbocyclic group or a substitutedor unsubstituted C₁-C₆₀ heterocyclic group,

at least one substituent of the substituted C₅-C₆₀ carbocyclic group,the substituted C₁-C₆₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₁-C₆₀ heteroaryl group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

Another aspect of embodiments of the present disclosure provides anorganic light-emitting device including: a first electrode; a secondelectrode facing the first electrode; and an organic layer between thefirst electrode and the second electrode and including an emissionlayer, wherein the organic layer includes at least one heterocycliccompound represented by Formula 1.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects of embodiments will become apparent and morereadily appreciated from the following description of the embodiments,taken in conjunction with the accompanying drawings in which:

FIG. 1 is a schematic view of an organic light-emitting device accordingto an embodiment;

FIG. 2 is a schematic view of an organic light-emitting device accordingto an embodiment;

FIG. 3 is a schematic view of an organic light-emitting device accordingto an embodiment; and

FIG. 4 is a schematic view of an organic light-emitting device accordingto an embodiment.

DETAILED DESCRIPTION

Reference will now be made in more detail to embodiments, examples ofwhich are illustrated in the accompanying drawings, wherein likereference numerals refer to like elements throughout. In this regard,the present embodiments may have different forms and should not beconstrued as being limited to the descriptions set forth herein.Accordingly, the embodiments are merely described below, by referring tothe figures, to explain aspects of embodiments of the presentdescription. As used herein, the term “and/or” includes any and allcombinations of one or more of the associated listed items. Expressionssuch as “at least one of,” when preceding a list of elements, modify theentire list of elements and do not modify the individual elements of thelist.

A heterocyclic compound according to an embodiment is represented byFormula 1:

In Formula 1, Y₁ may be N or P.

In one embodiment, Y₁ may be N.

In Formula 1, Y₂ may be B(R₁), P(═O)(R₁), or P(═S)(R₁).

In Formula 1, X₁ and X₂ may each independently be O, S, N(R₂),C(R₂)(R₃), or Si(R₂)(R₃).

a10, a20, and a30 may each independently be selected from 0, 1, 2, 3, 4,5, 6, 7, and 8,

In Formula 1, m1 and m2 may each independently be 0, 1, or 2, wherem1+m2>0.

When m1 is 0, —(X₁)_(m1)—may not exist (e.g., may not be included). Forexample, when m1 is 0, the heterocyclic compound may be represented byFormula 1-1:

When m2 is 0, —(X₂)_(m2)—may not exist (e.g., may not be included). Forexample, when m2 is 0, the heterocyclic compound may be represented byFormula 1-2:

In Formulae 1-1 and 1-2, Y₁, Y₂, X₁, X₂, m1, m2, A₁ to A₃, R₁₀, R₂₀,R₃₀, a10, a20, and a30 may each independently be the same as describedherein.

In one embodiment, in Formula 1, m1 may be 1, and m2 may be 0 or 1.

In Formula 1, A₁ to A₃ may each independently be a substituted orunsubstituted C₅-C₆₀ carbocyclic group or a substituted or unsubstitutedC₁-C₆₀ heterocyclic group.

In one embodiment, in Formula 1, A₁ and A₂ may each independently beselected from a benzene group, a naphthalene group, a phenanthrenegroup, an anthracene group, a triphenylene group, a pyrene group, achrysene group, a pyridine group, a pyrazine group, a pyrimidine group,a triazine group, a quinoline group, an isoquinoline group, abenzoquinoline group, a benzoisoquinoline group, a 2,6-naphthyridinegroup, a 1,8-naphthyridine group, a 1,5-naphthyridine group, a1,6-naphthyridine group, a 1,7-naphthyridine group, a 2,7-naphthyridinegroup, a quinoxaline group, a quinazoline group, a phenanthridine group,and a phenanthroline group.

In one embodiment, A₃ may be selected from a benzene group, anaphthalene group, a phenanthrene group, an anthracene group, atriphenylene group, a pyrene group, a chrysene group, a pyridine group,a pyrazine group, a pyrimidine group, a triazine group, a quinolinegroup, an isoquinoline group, a benzoquinoline group, abenzoisoquinoline group, a 2,6-naphthyridine group, a 1,8-naphthyridinegroup, a 1,5-naphthyridine group, a 1,6-naphthyridine group, a1,7-naphthyridine group, a 2,7-naphthyridine group, a quinoxaline group,a quinazoline group, a phenanthridine group, a phenanthroline group, abenzofuran group, a benzothiophene group, an indene group, an indolegroup, a furopyridine group, a thienopyridine group, acyclopentapyridine group, a pyrrolopyridine group, a dibenzofuran group,a dibenzothiophene group, a fluorene group, a carbazole group, abenzonaphthofuran group, a benzonaphthothiophene group, a benzofluorenegroup, a benzocarbazole group, a dinaphthofuran group, adinaphthothiophene group, a dibenzofluorene group, a dibenzocarbazolegroup, a benzoxazole group, a benzothiazole group, a benzimidazolegroup, a naphthofuran, a naphthothiophene, a spiro-bifluorene group, anda spiro-fluorene-indene group; and

a group represented by Formula 1A:

In Formula 1A,

Y₂₁ may be N or P,

Y₂₂ may be B(R₄), P(═O)(R₄), or P(═S)(R₄),

X₂₁ and X₂₂ may each independently be O, S, N(R₅), C(R₅)(R₆), orSi(R₅)(R₆),

m21 and m22 may each independently be 0, 1, or 2, and may satisfym21+m22>0,

A₂₁ to A₂₃ may each independently be a substituted or unsubstitutedC₅-C₆₀ carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

a40, a50, and a60 may be the same as defined in connection with a10,a20, and a30,

R₄ may be the same as defined in connection with R₁,

R₅ and R₆ may each independently be the same as defined in connectionwith R₂ and R₃, and

R₄₀, R₅₀, and R₆₀ may each independently be the same as defined inconnection with R₁₀, R₂₀, and R₃₀.

For example, R₄ to R₆, R₄₀, R₅₀, and R₆₀ may optionally be linked toform a substituted or unsubstituted C₅-C₆₀ carbocyclic group or asubstituted or unsubstituted C₁-C₆₀ heterocyclic group.

In one embodiment, the heterocyclic compound represented by Formula 1may be represented by one selected from Formulae 2-1 to 2-3:

In Formulae 2-1 to 2-3,

Y₁, Y₂, X₁, and X₂ may each independently be the same as describedherein,

Y₂₁ may be N or P,

Y₂₂ may be B(R₄), P(═O)(R₄), or P(═S)(R₄),

X₂₁ may be O, S, N(R₅), C(R₅)(R₆), or Si(R₅)(R₆),

A₁₁ to A₁₃ and A₂₁ to A₂₃ may each independently be selected from abenzene group, a naphthalene group, a phenanthrene group, an anthracenegroup, a triphenylene group, a pyrene group, a chrysene group, apyridine group, a pyrazine group, a pyrimidine group, a triazine group,a quinoline group, an isoquinoline group, a benzoquinoline group, abenzoisoquinoline group, a quinoxaline group, a quinazoline group, aphenanthridine group, a phenanthroline group, a dibenzofuran group, adibenzothiophene group, a fluorene group, a carbazole group, abenzonaphthofuran group, a benzonaphthothiophene group, a benzofluorenegroup, and a benzocarbazole group,

a10, a20, a30, a40, a50, and a60 may be the same as described herein,

R₁₀, R₂₀, and R₃₀ may each independently be the same as describedherein,

R₄ may be the same as defined in connection with

R₅ and R₆ may each independently be the same as defined in connectionwith R₂ and R₃, and

R₄₀, R₅₀, and R₆₀ may each independently be the same as defined inconnection with R₁₀, R₂₀, and R₃₀.

In one embodiment, the heterocyclic compound represented by Formula 1may be represented by one selected from Formulae 10-1 to 10-17:

In Formulae 10-1 to 10-17,

Y₁, Y₂, X₁, and X₂ may each independently be the same as describedherein,

R₁₁ to R₁₅ may each independently be the same as defined in connectionwith R₁₀,

R₂₁ to R₂₆ may each independently be the same as defined in connectionwith R₂₀,

R₃₁ to R₃₆ may each independently be the same as defined in connectionwith R₃₀,

Y₂₁ may be N or P,

Y₂₂ may be B(R₄), P(═O)(R₄), or P(═S)(R₄),

X₂₁ may be C(R₅)(R₆) or Si(R₅)(R₆),

R₄ may be the same as defined in connection with R₁,

R₅ and R₆ may each independently be the same as defined in connectionwith R₂ and R₃,

R₄₁ to R₄₃ may each independently be the same as defined in connectionwith R₁₀,

R₅₁ to R₅₄ may each independently be the same as defined in connectionwith R₂₀,

R₆₁ and R₆₂ may each independently be the same as defined in connectionwith R₃₀, and

two or more neighboring substituents selected from R₁₁ to R₁₅, R₂₁ toR₂₆, R₃₁ to R₃₆, R₄₁ to R₄₃, R₅₁ to R₅₄, R₆₁, and R₆₂ may optionally belinked to form a benzene group or a naphthalene group.

In Formula 1, R₁ to R₃, R₁₀, R₂₀, and R₃₀ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —C(═O)(Q₁),—N(Q₁)(Q₂), —P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁)(Q₂),

R₁ to R₃, R₁₀, R₂₀, and R₃₀ may optionally be linked to form asubstituted or unsubstituted C₅-C₆₀ carbocyclic group or a substitutedor unsubstituted C₁-C₆₀ heterocyclic group.

In one embodiment, R₁ to R₃ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₆-C₆₀aryl group, —Si(Q₁)(Q₂)(Q₃), and —N(Q₁)(Q₂),

Q₁ to Q₃ may each independently be selected from hydrogen, deuterium, aC₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, and

R₂ and R₃ may be linked to form a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀ heterocyclicgroup.

In one embodiment, R₁ to R₃ may each independently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group,an n-propyl group, an isopropyl group, an n-butyl group, a sec-butylgroup, an isobutyl group, a tert-butyl group, an ethenyl group, apropenyl group, a butenyl group, a methoxy group, an ethoxy group, ann-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxygroup, an isobutoxy group, and a tert-butoxy group;

a methyl group, an ethyl group, an n-propyl group, an isopropyl group,an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butylgroup, a methoxy group, an ethoxy group, an n-propoxy group, anisopropoxy group, an n-butoxy group, a sec-butoxy group, an isobutoxygroup, and a tert-butoxy group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a cyano group, a phenylgroup, and a biphenyl group;

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, and a pentacenyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, and apentacenyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethylgroup, an n-propyl group, an isopropyl group, an n-butyl group, asec-butyl group, an isobutyl group, a tert-butyl group, a methoxy group,an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxygroup, a sec-butoxy group, an isobutoxy group, and a tert-butoxy group;and

—N(Q₁)(Q₂), and

R₂ and R₃ may optionally be linked to form a group represented by oneselected from Formulae 9-1 and 9-2:

In Formulae 9-1 and 9-2,

X₁₁ may be C or Si,

when X₁ in Formula 1 is C(R₂)(R₃), X₁₁ may be C, and when X₁ in Formula1 is Si(R₂)(R₃), X₁₁ may be Si,

X₉₁ and X₉₃ may each independently be selected from a single bond, O, S,Se, N(R₉₄), B(R₉₄), P(═O)(R₉₄), P(═S)(R₉₄), C(R₉₄)(R₉₅), Si(R₉₄)(R₉₅),and Ge(R₉₄)(R₉₅),

X₉₂ may be selected from N, B, and P,

A₉₁ to A₉₃ may each independently be selected from a C₅-C₃₀ carbocyclicgroup and a C₁-C₃₀ heterocyclic group,

R₉₁ to R₉₅ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and—P(═O)(Q₁)(Q₂),

Q₁ to Q₃ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a phenyl group, a biphenyl group, a terphenyl group, a fluorenylgroup, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a naphthyridinyl group, a quinoxalinyl group, a quinazolinylgroup, a carbazolyl group, a phenanthridinyl group, an acridinyl group,a phenanthrolinyl group, a phenazinyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, and aterphenyl group, and

b91 to b93 may each independently be an integer from 1 to 10.

In one embodiment, when R₅ and R₆ in Formula 1A are linked to form asubstituted or unsubstituted C₅-C₆₀ carbocyclic group or a substitutedor unsubstituted C₁-C₆₀ heterocyclic group, R₅ and R₆ may be also linkedto form a group represented by one selected from Formulae 9-1 and 9-2.

In one embodiment, A₉₁ to A₉₃ in Formulae 9-1 and 9-2 may eachindependently be selected from a benzene group, a naphthalene group, aphenanthrene group, an anthracene group, a pyridine group, a pyrazinegroup, a pyrimidine group, a quinoline group, an isoquinoline group, abenzoquinoline group, a benzoisoquinoline group, a dibenzofuran group, adibenzothiophene group, a fluorene group, and a carbazole group.

In one embodiment, R₁₀, R₂₀, and R₃₀ may each independently be selectedfrom hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a substitutedor unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstitutedC₆-C₆₀ aryl group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), and —N(Q₁)(Q₂), and

Q₁ to Q₃ may each independently be selected from hydrogen, deuterium, aC₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

In one embodiment, R₁₀, R₂₀, and R₃₀ may each independently be selectedfrom:

hydrogen, deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group,an n-propyl group, an isopropyl group, an n-butyl group, a sec-butylgroup, an isobutyl group, a tert-butyl group, an ethenyl group, apropenyl group, a butenyl group, a methoxy group, an ethoxy group, ann-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxygroup, an isobutoxy group, and a tert-butoxy group;

a methyl group, an ethyl group, an n-propyl group, an isopropyl group,an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butylgroup, a methoxy group, an ethoxy group, an n-propoxy group, anisopropoxy group, an n-butoxy group, a sec-butoxy group, an isobutoxygroup, and a tert-butoxy group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a cyano group, a phenylgroup, and a biphenyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, apentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group,a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group,a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, abenzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group,a triazolyl group, a tetrazolyl group, a thiadiazolyl group, anoxadiazolyl group, a triazinyl group, a carbazolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a benzocarbazolyl group, a naphthobenzofuranyl group, anaphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenylgroup, a dinaphtho silolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinylgroup, a benzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, an indolopyrrolyl group, an indeno carbazolylgroup, and an indolocarbazolyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, apentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group,a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group,a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, abenzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group,a triazolyl group, a tetrazolyl group, a thiadiazolyl group, anoxadiazolyl group, a triazinyl group, a carbazolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a benzocarbazolyl group, a naphthobenzofuranyl group, anaphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenylgroup, a dinaphtho silolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinylgroup, a benzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, an indolopyrrolyl group, an indeno carbazolylgroup, and an indolocarbazolyl group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a cyano group, a methylgroup, an ethyl group, an n-propyl group, an isopropyl group, an n-butylgroup, a sec-butyl group, an isobutyl group, a tert-butyl group, amethoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group,an n-butoxy group, a sec-butoxy group, an isobutoxy group, tert-butoxygroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, apentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group,a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group,a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, abenzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group,a triazolyl group, a tetrazolyl group, a thiadiazolyl group, anoxadiazolyl group, a triazinyl group, a carbazolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a benzocarbazolyl group, a naphthobenzofuranyl group, anaphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenylgroup, a dinaphtho silolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinylgroup, a benzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, an indolopyrrolyl group, an indeno carbazolylgroup, an indolocarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂),and —P(═S)(Q₃₁)(Q₃₂), and

—N(Q₁₁)(Q₁₂), and

R₁₀, R₂₀, and R₃₀ may optionally be linked to form a substituted orunsubstituted C₅-C₆₀ carbocyclic group or a substituted or unsubstitutedC₁-C₆₀ heterocyclic group.

In one embodiment, R₁₀, R₂₀, and R₃₀ may each independently be selectedfrom:

hydrogen, deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group,an n-propyl group, an isopropyl group, an n-butyl group, a sec-butylgroup, an isobutyl group, a tert-butyl group, an ethenyl group, apropenyl group, a butenyl group, a methoxy group, an ethoxy group, ann-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxygroup, an isobutoxy group, and a tert-butoxy group; and

a group represented by one selected from Formulae 5-1 to 5-26 andFormulae 6-1 to 6-55:

In Formulae 5-1 to 5-26 and Formulae 6-1 to 6-55,

Y₃₁ and Y₃₂ may be O, S, C(Z₃₄)(Z₃₅), N(Z₃₄), or Si(Z₃₄)(Z₃₅),

Z₃₁, Z₃₂, Z₃₄, and Z₃₅ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, aphenanthrenyl group, an anthracenyl group, a triphenylenyl group, apyridinyl group, a pyrimidinyl group, a carbazolyl group, and atriazinyl group,

e2 may be 1 or 2,

e3 may be an integer from 1 to 3,

e4 may be an integer from 1 to 4,

e5 may be an integer from 1 to 5,

e6 may be an integer from 1 to 6,

e7 may be an integer from 1 to 7,

e9 may be an integer from 1 to 9, and

* indicates a binding site to a neighboring atom.

At least one substituent of the substituted C₅-C₆₀ carbocyclic group,the substituted C₁-C₆₀ heterocyclic group, the substituted C₁-C₆₀ alkylgroup, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substitutedC₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀ heterocycloalkyl group,the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, thesubstituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group,the substituted C₁-C₆₀ heteroaryl group, the substituted C₁-C₆₀heteroaryloxy group, the substituted C₁-C₆₀ heteroarylthio group, thesubstituted monovalent non-aromatic condensed polycyclic group, and thesubstituted monovalent non-aromatic condensed heteropolycyclic group maybe selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

In one embodiment, the heterocyclic compound may be selected fromCompounds 1 to 165:

The heterocyclic compound may have an asymmetric structure with respectto the Y₁ atom in Formula 1, may have a three-dimensionally bulkystructure, and may control formation of excimer or exciplex due to asteric effect, thereby improving the efficiency of the organiclight-emitting device when included therein by, for example, reducingDexter energy transfer.

For example, Dexter energy transfer is a mechanism that provides a paththrough which triplet excitons primarily move, and, as a result ofDexter energy transfer, electrons directly hop. Dexter energy transferis a phenomenon that may easily occur when an inter-molecular distanceis short. While the present application is not limited by any particularmechanism or theory, it is believed that because the heterocycliccompound according to the embodiment has a structure that may widen theinter-molecular distance, and thus, the Dexter energy transfer may besuppressed or reduced. Consequently, a disadvantageous effect caused byhopping of triplet exciton may be suppressed or reduced.

In addition, the heterocyclic compound may include substituents havingproperties of an electron withdrawing group (EWG) and/or an electrondonating group (EDG). By introducing these substituents at suitable orappropriate positions, an energy difference between a singlet state anda triplet state of an entire compound may be suitably or appropriatelyadjusted. In this manner, the heterocyclic compound may exhibitthermally activated delayed fluorescence (TADF).

Singlet energy (S1) and triplet energy (T1) of the heterocyclic compoundmay satisfy the following equation:

ΔE _(st) =S1−T1≤0.3 eV.

In one embodiment, the heterocyclic compound includes the structure ofFormula 1 and includes Y₁, which is an N atom or a P atom, and Y₂, whichis B(R₁), P(═O)(R₁), or P(═S)(R₁), a highest occupied molecular orbital(HOMO) and a lowest unoccupied molecular orbital (LUMO) may be separatedby multiple resonances. Therefore, the heterocyclic compound exhibitsTADF characteristics, has high luminescent efficiency because theoverlap of HOMO and LUMO is large, and has a small full width at halfmaximum (FWHM) and a small Stokes shift because a change in structurebefore the transition is small. In addition, when an electron donor type(or kind of) substituent is introduced into the heterocyclic compound,these characteristics may be further reinforced or improved.

In one embodiment, because the HOMO and the LUMO are separated accordingto the structure of the substituent included in the heterocycliccompound, it is possible to control the heterocyclic compound so thatbehavior characteristics of a general TADF material are exhibitedinstead of the multiple resonances. For example, the core structurerepresented by Formula 1 is included as an electron acceptor moiety, andat least one selected from R₁ to R₃, R₁₀, R₂₀, and R₃₀, which are thesubstituents of the core structure is included as an electron donormoiety. Therefore, charges are easily moved in the molecules of theheterocyclic compound, thereby improving the luminescent efficiency. Inaddition, a dipole is formed from the electron donor moiety to theelectron acceptor moiety, and a dipole moment of the molecule of theheterocyclic compound is increased, thereby further improving theluminous efficiency.

In addition, in the heterocyclic compound, because the electron donormoiety and the electron acceptor moiety are separated, inter-molecularorbital overlap may be effectively prevented or reduced. Therefore, theheterocyclic compound may have low ΔE_(st) and intersystem crossing to asinglet excited state is enabled even at room temperature throughthermal activation from a triplet excited state. Therefore, theheterocyclic compound may exhibit delayed fluorescence and an exciton ofa triplet state may be used for light emission, thereby improving theluminescent efficiency.

Furthermore, because the heterocyclic compound has a relatively highcharge (hole or electron) transport capability, it is possible toimprove an exciton forming ratio in the emission layer of the organiclight-emitting device by including the heterocyclic compound representedby Formula 1. Therefore, the organic light-emitting device may have alow driving voltage, high efficiency, a long lifespan, and high maximumquantum efficiency. In some embodiments, the emission layer does notinclude an organometallic compound. For example, the emission layer maybe free or substantially free of organometallic compounds. As usedherein, the statement “substantially free of organometallic compounds”means that organometallic compounds are present, if at all, only as anincidental impurity and do not materially affect the emissioncharacteristics of the emission layer.

A synthesis method for the heterocyclic compound represented by Formula1 would be apparent to those of ordinary skill in the art by referringto the following examples.

At least one heterocyclic compound of Formula 1 may be used between apair of electrodes of an organic light-emitting device. For example, theheterocyclic compound may be included in at least one layer selectedfrom a hole transport region, an electron transport region, and anemission layer. In one or more embodiments, the heterocyclic compound ofFormula 1 may be used as a material for a capping layer located outsidea pair of electrodes of an organic light-emitting device.

Accordingly, provided is an organic light-emitting device including afirst electrode; a second electrode facing the first electrode, and anorganic layer that is between the first electrode and the secondelectrode and includes at least one the heterocyclic compound of Formula1 described above.

The expression “(an organic layer) includes at least one heterocycliccompound” as used herein may include a case in which “(an organic layer)includes identical heterocyclic compound represented by Formula 1” or acase in which “(an organic layer) includes two or more differentheterocyclic compounds represented by Formula 1”.

For example, the organic layer may include, as the heterocycliccompound, only Compound 1. In this regard, Compound 1 may exist only inthe emission layer of the organic light-emitting device. In one or moreembodiments, the organic layer may include, as the heterocycliccompound, Compound 1 and Compound 2. In this regard, Compound 1 andCompound 2 may exist in an identical layer (for example, Compound 1 andCompound 2 may all exist in an emission layer), or different layers (forexample, Compound 1 may exist in an emission layer and Compound 2 mayexist in an electron transport layer).

In one embodiment, the first electrode may be an anode, and the secondelectrode may be a cathode, and the organic layer may further include ahole transport region between the first electrode and the emission layerand an electron transport region between the emission layer and thesecond electrode, wherein the hole transport region may include a holeinjection layer, a hole transport layer, an emission auxiliary layer, anelectron blocking layer, or any combination thereof, and

the electron transport region may include a hole blocking layer, anelectron transport layer, an electron injection layer, or anycombination thereof.

In one or more embodiments, the emission layer of the organiclight-emitting device may include the heterocyclic compound.

In one or more embodiments, the emission layer of the organiclight-emitting device may include the heterocyclic compound, theheterocyclic compound included in the emission layer may be a thermallyactivated delayed fluorescence (TADF) emitter, and the emission layermay emit delayed fluorescence.

In one or more embodiments, the emission layer may include (or consistof) the heterocyclic compound; or the emission layer may further includea host, and an amount of the heterocyclic compound may be in a range ofabout 0.1 parts by weight to about 50 parts by weight based on 100 partsby weight of the emission layer.

For example, the emission layer may consist of the heterocycliccompound, and the heterocyclic compound may be a TADF emitter, and theTADF may satisfy Equation 1:

|E _(D, S1) −E _(D, T1)|≤0.3 eV.   Equation 1

In Equation 1,

E_(D, S1) is singlet energy (eV) of the TADF emitter, and

E_(D, T1) is triplet energy (eV) of the TADF emitter.

Because a difference between the singlet energy (E_(D, S1)) and thetriplet energy (E_(D, T1)) of the TADF emitter, e.g., the heterocycliccompound represented by Formula 1 is 0.3 eV or less, singlet stateexcitons and triplet state excitons generated by an electric field mayeasily transit to an intermediate state, and thus, the organiclight-emitting device including the heterocyclic compound may haveexcellent luminescent efficiency.

In one or more embodiments, the emission layer may include theheterocyclic compound and the host, the heterocyclic compound may be aTADF emitter, and the TADF emitter and the host may satisfy Equation 2or 3:

|E _(H, HOMO) −E _(D, HOMO)|≤0.5 eV   Equation 2

|E _(H, LUMO) −E _(D, LUMO)|≤0.5 eV.   Equation 3

In Equations 2 and 3,

E_(H, HOMO) is a HOMO level (e.g., a HOMO energy level) of the host,

E_(D, HOMO) is a HOMO level (e.g., a HOMO energy level) of the TADFemitter,

E_(H, LUMO) is a LUMO level (e.g., a LUMO energy level) of the host, and

E_(D, LUMO) is a LUMO level (e.g., a LUMO energy level) of the TADFemitter.

Because a difference in HOMO level or LUMO level between the TADFemitter, e.g., the heterocyclic compound represented by Formula 1, andthe host is 0.5 eV or less, charge movement from the host to the TADFemitter may be facilitated, and thus, the organic light-emitting deviceincluding the heterocyclic compound and the host may have excellentluminescent efficiency.

The host in the emission layer may include at least one selected from ananthracene-based compound, a pyrene-based compound, aspiro-bifluorene-based compound, a carbazole-based compound, abenzimidazole-based compound, and a phosphine oxide-based compound.

According to an embodiment, the host may be one selected from CompoundsH101 to H106 below:

In one embodiment, the emission layer of the organic light-emittingdevice may include the heterocyclic compound, and the emission layer mayemit blue light having a maximum emission wavelength of 430 nm or moreand 480 nm or less.

In one embodiment, the hole transport region of the organiclight-emitting device may include a p-dopant which has a lowestunoccupied molecular orbital (LUMO) energy level of −3.5 eV or less.

In one embodiment, the electron transport region of the organiclight-emitting device may include at least one selected from a phosphineoxide-based compound and a benzimidazole-based compound, and may furtherinclude an alkali metal, an alkaline earth metal, a rare earth metal, analkali metal compound, an alkaline earth-metal compound, a rare earthmetal compound, an alkali metal complex, an alkaline earth-metalcomplex, a rare earth metal complex, or any combinations thereof.

The term “organic layer,” as used herein, refers to a single layerand/or a plurality of layers between the first electrode and the secondelectrode of the organic light-emitting device. A material included inthe “organic layer” is not limited to an organic material. For example,the organic layer may include an inorganic material.

Description of FIG. 1

FIG. 1 is a schematic cross-sectional view of an organic light-emittingdevice 10 according to an embodiment. The organic light-emitting device10 includes a first electrode 110, an organic layer 150, and a secondelectrode 190.

Hereinafter, the structure of the organic light-emitting device 10according to an embodiment and a method of manufacturing the organiclight-emitting device 10 will be described in connection with FIG. 1.

First Electrode 110

In FIG. 1, a substrate may be additionally under the first electrode 110or above the second electrode 190. The substrate may be a glasssubstrate or a plastic substrate, each having excellent mechanicalstrength, thermal stability, transparency, surface smoothness, ease ofhandling, and water resistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode 110 on the substrate. When thefirst electrode 110 is an anode, the material for forming the firstelectrode 110 may be selected from materials having a high work functionto facilitate hole injection.

The first electrode 110 may be a reflective electrode, a semi-reflectiveelectrode, or a transmissive electrode. When the first electrode 110 isa transmissive electrode, a material for forming a first electrode maybe selected from indium tin oxide (ITO), indium zinc oxide (IZO), tinoxide (SnO₂), zinc oxide (ZnO), and any combinations thereof, butembodiments of the present disclosure are not limited thereto. In one ormore embodiments, when the first electrode 110 is a semi-transmissiveelectrode or a reflective electrode, a material for forming a firstelectrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum(Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In),magnesium-silver (Mg—Ag), and any combinations thereof, but embodimentsof the present disclosure are not limited thereto.

The first electrode 110 may have a single-layered structure, or amulti-layered structure including two or more layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO,but the structure of the first electrode 110 is not limited thereto.

Organic Layer 150

The organic layer 150 may be on the first electrode 110. The organiclayer 150 may include an emission layer.

The organic layer 150 may further include a hole transport regionbetween the first electrode 110 and the emission layer and an electrontransport region between the emission layer and the second electrode190.

Hole Transport Region in Organic Layer 150

The hole transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The hole transport region may include at least one layer selected from ahole injection layer, a hole transport layer, an emission auxiliarylayer, and an electron blocking layer.

For example, the hole transport region may have a single-layeredstructure including a single layer including a plurality of differentmaterials, or a multi-layered structure having a hole injectionlayer/hole transport layer structure, a hole injection layer/holetransport layer/emission auxiliary layer structure, a hole injectionlayer/emission auxiliary layer structure, a hole transportlayer/emission auxiliary layer structure, or a hole injection layer/holetransport layer/electron blocking layer structure, wherein for eachstructure, constituting layers are sequentially stacked from the firstelectrode 110 in this stated order, but the structure of the holetransport region is not limited thereto.

In one embodiment, the hole transport region may include at least oneselected from m-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, Spiro-TPD,Spiro-NPB, methylated-NPB, TAPC, HMTPD,4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzenesulfonic acid (PAN I/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound representedby Formula 201, and a compound represented by Formula 202:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

L₂₀₅ may be selected from *—O—*′, *—S—*′, *—N(Q₂₀₁)—*′, a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₂-C₂₀ alkenylene group, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be an integer from 0 to 3,

xa5 may be an integer from 1 to 10, and

R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independently be selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 202, R₂₀₁ and R₂₀₂ may optionally be linked viaa single bond, a dimethyl-methylene group, or a diphenyl-methylenegroup, and R₂₀₃ and R₂₀₄ may optionally be linked via a single bond, adimethyl-methylene group, or a diphenyl-methylene group.

In one embodiment, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xa1 to xa4 may each independently be 0, 1,or 2.

In one or more embodiments, xa5 may be 1, 2, 3, or 4.

In one or more embodiments, R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independentlybe selected from:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above.

In one or more embodiments, at least one selected from R₂₀₁ to R₂₀₃ inFormula 201 may each independently be selected from:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a phenyl group substituted with a C₁-C₁₀ alkylgroup, a phenyl group substituted with —F, a naphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formula 202, i) R₂₀₁ and R₂₀₂ may belinked via a single bond, and/or ii) R₂₀₃ and R₂₀₄ may be linked via asingle bond.

In one or more embodiments, at least one selected from R₂₀₁ to R₂₀₄ inFormula 202 may each independently be selected from:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, acarbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

The compound represented by Formula 201 may be represented by Formula201A:

For example, the compound represented by Formula 201 may be representedby Formula 201A(1), but embodiments of the present disclosure are notlimited thereto:

In one embodiment, the compound represented by Formula 201 may berepresented by Formula 201A-1, but embodiments of the present disclosureare not limited thereto:

In one embodiment, the compound represented by Formula 202 may berepresented by Formula 202A:

In one or more embodiments, the compound represented by Formula 202 maybe represented by Formula 202A-1:

In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1,

L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ are the same asdescribed above,

R₂₁₁ and R₂₁₂ may each independently be the same as defined inconnection with R₂₀₃, and

R₂₁₃ to R₂₁₇ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group.

The hole transport region may include at least one compound selectedfrom Compounds HT1 to HT39, but embodiments of the present disclosureare not limited thereto:

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes at least one selected from a holeinjection layer and a hole transport layer, the thickness of the holeinjection layer may be in a range of about 100 Å to about 9,000 Å, andfor example, about 100 Å to about 1,000 Å, and the thickness of the holetransport layer may be in a range of about 50 Å to about 2,000 Å, andfor example, about 100 Å to about 1500 Å. When the thicknesses of thehole transport region, the hole injection layer, and the hole transportlayer are within these ranges, suitable or satisfactory holetransporting characteristics may be obtained without a substantialincrease in driving voltage.

The emission auxiliary layer may increase light-emission efficiency bycompensating for an optical resonance distance according to thewavelength of light emitted by an emission layer, and the electronblocking layer may block the flow of electrons from an electrontransport region. The emission auxiliary layer and the electron blockinglayer may include the materials as described above.

p-Dopant

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant.

In one embodiment, the p-dopant may have a LUMO energy level of −3.5 eVor less.

The p-dopant may include at least one selected from a quinonederivative, a metal oxide, and a cyano group-containing compound, butembodiments of the present disclosure are not limited thereto.

In one embodiment, the p-dopant may include at least one selected from:

a quinone derivative, such as tetracyanoquinodimethane (TCNQ) or2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

a metal oxide, such as tungsten oxide or molybdenum oxide;

1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221 below,

but embodiments of the present disclosure are not limited thereto:

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, wherein at least oneselected from R₂₂₁ to R₂₂₃ may have at least one substituent selectedfrom a cyano group, —F, —Cl, —Br, —I, a C₁-C₂₀ alkyl group substitutedwith —F, a C₁-C₂₀ alkyl group substituted with —Cl, a C₁-C₂₀ alkyl groupsubstituted with —Br, and a C₁-C₂₀ alkyl group substituted with -I.

Emission Layer in Organic Layer 150

When the organic light-emitting device 10 is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, or a blue emission layer,according to a sub-pixel. In one or more embodiments, the emission layermay have a stacked structure of two or more layers selected from a redemission layer, a green emission layer, and a blue emission layer, inwhich the two or more layers contact each other or are separated fromeach other. In one or more embodiments, the emission layer may includetwo or more materials selected from a red light-emitting material, agreen light-emitting material, and a blue light-emitting material, inwhich the two or more materials are mixed with each other in a singlelayer to emit white light.

The emission layer may include a host and a dopant. The dopant mayinclude at least one selected from a phosphorescent dopant and afluorescent dopant.

An amount of the dopant in the emission layer may be in a range of about0.01 parts by weight to about 15 parts by weight based on 100 parts byweight of the host, but embodiments of the present disclosure are notlimited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

Host in Emission Layer

In one or more embodiments, the host may include a compound representedby Formula 301 below:

[Ar₃₀₁]_(xb11)−[(L₃₀₁)_(xb1)−R₃₀₁]_(xb21).   Formula 301

In Formula 301,

Ar₃₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xb1 may be an integer from 0 to 5,

R₃₀₁ may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), and —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5, and

Q₃₀₁ to Q₃₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group, but embodiments of the presentdisclosure are not limited thereto.

In one embodiment, Ar₃₀₁ in Formula 301 may be selected from:

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup; and

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group, but embodiments of the present disclosureare not limited thereto.

In Formula 301, when xb11 is two or more, two or more Ar₃₀₁(s) may belinked via a single bond.

In one or more embodiments, the compound represented by Formula 301 maybe represented by Formula 301-1 or 301-2:

In Formulae 301-1 and 301-2,

A₃₀₁ to A₃₀₄ may each independently be a benzene group, a naphthalenegroup, a phenanthrene group, a fluoranthene group, a triphenylene group,a pyrene group, a chrysene group, a pyridine group, a pyrimidine group,an indene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, an indole group, acarbazole group, a benzocarbazole group, a dibenzocarbazole group, afuran group, a benzofuran group, a dibenzofuran group, a naphthofurangroup, a benzonaphthofuran group, a dinaphthofuran group, a thiophenegroup, a benzothiophene group, a dibenzothiophene group, anaphthothiophene group, a benzonaphthothiophene group, and adinaphthothiophene group,

X₃₀₁ may be O, S, or N-[(L₃₀₄)_(xb4)−R₃₀₄],

R₃₁₁ to R₃₁₄ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, R₃₀₁, and Q₃₁ to Q₃₃ are the same as described above,

L₃₀₂ to L₃₀₄ may each independently be the same as defined in connectionwith L₃₀₁,

xb2 to xb4 may each independently be the same as defined in connectionwith xb1, and

R₃₀₂ to R₃₀₄ may each independently be the same as defined in connectionwith R₃₀₁.

For example, in Formulae 301, 301-1, and 301-2, L₃₀₁ to L₃₀₄ may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above.

In one embodiment, in Formulae 301, 301-1, and 301-2, R₃₀₁ to R₃₀₄ mayeach independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above.

In one or more embodiments, the host may include an alkaline earth metalcomplex. For example, the host may be selected from a Be complex (forexample, Compound H55), a Mg complex, and a Zn complex.

The host may include at least one selected from9,10-di(2-naphthyl)anthracene (ADN),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene(mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55,but embodiments of the present disclosure are not limited thereto:

Phosphorescent Dopant Included in Emission Layer in Organic Layer 150

The phosphorescent dopant may include an organometallic complexrepresented by Formula 401 below:

In Formulae 401 and 402,

M may be selected from iridium (Ir), platinum (Pt), palladium (Pd),osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),terbium (Tb), rhodium (Rh), and thulium (Tm),

L₄₀₁ may be selected from ligands represented by Formula 402, and xc1may be 1, 2, or 3, wherein, when xc1 is two or more, two or more L₄₀₁(s)may be identical to or different from each other,

L₄₀₂ may be an organic ligand, and xc2 may be an integer from 0 to 4,wherein, when xc2 is two or more, two or more L₄₀₂(s) may be identicalto or different from each other,

X₄₀₁ to X₄₀₄ may each independently be nitrogen or carbon,

X₄₀₁ and X₄₀₃ may be linked via a single bond or a double bond, and X₄₀₂and X₄₀₄ may be linked via a single bond or a double bond,

A₄₀₁ and A₄₀₂ may each independently be selected from a C₅-C₆₀carbocyclic group or a C₁-C₆₀ heterocyclic group,

X₄₀₅ may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)—*′,*—C(Q₄₁₁)(Q₄₁₂)—*′, *—C(Q₄₁₁)═C(Q₄₁₂)—*′, *—C(Q₄₁₁)═*′, or *═C═*′,wherein Q₄₁₁ and Q₄₁₂ may be hydrogen, deuterium, a C₁-C₂₀ alkyl group,a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, or a naphthyl group,

X₄₀₆ may be a single bond, O, or S,

R₄₀₁ and R₄₀₂ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₁-C₂₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂),—B(Q₄o1)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂),wherein Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a C₆-C₂₀ aryl group, and a C₁-C₂₀heteroaryl group,

xc11 and xc12 may each independently be an integer from 0 to 10, and

* and *′ in Formula 402 each indicate a binding site to M in Formula401.

In one embodiment, A₄₀₁ and A₄₀₂ in Formula 402 may each independentlybe selected from a benzene group, a naphthalene group, a fluorene group,a spiro-bifluorene group, an indene group, a pyrrole group, a thiophenegroup, a furan group, an imidazole group, a pyrazole group, a thiazolegroup, an isothiazole group, an oxazole group, an isoxazole group, apyridine group, a pyrazine group, a pyrimidine group, a pyridazinegroup, a quinoline group, an isoquinoline group, a benzoquinoline group,a quinoxaline group, a quinazoline group, a carbazole group, abenzimidazole group, a benzofuran group, a benzothiophene group, anisobenzothiophene group, a benzoxazole group, an isobenzoxazole group, atriazole group, a tetrazole group, an oxadiazole group, a triazinegroup, a dibenzofuran group, and a dibenzothiophene group.

In one or more embodiments, in Formula 402, i) X₄₀₁ may be nitrogen, andX₄₀₂ may be carbon, or ii) X₄₀₁ and X₄₀₂ may each be nitrogen at thesame time.

In one or more embodiments, R₄₀₁ and R₄₀₂ in Formula 402 may eachindependently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group,a cyclohexyl group, an adamantly group, a norbornanyl group, and anorbornenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantly group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantly group, anorbornanyl group, a norbornenyl group a phenyl group, a biphenyl group,a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, an adamantly group, a norbornanylgroup, a norbornenyl group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and adibenzothiophenyl group; and

—Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁),—S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂), and

Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, and anaphthyl group, but are not limited thereto.

In one or more embodiments, when xc1 in Formula 401 is two or more, twoA₄₀₁(s) in two or more L₄₀₁(s) may optionally be linked via X₄₀₇, whichis a linking group, or two A₄₀₂(s) in two or more L₄₀₁(s) may optionallybe linked via X₄₀₈, which is a linking group (see Compounds PD1 to PD4and PD7). X₄₀₇ and X₄₀₈ may each independently be a single bond, *—O—*′,*—S—*′, *—C(═O)—*′, *—N(Q₄₁₃)—*′, *—C(Q₄₁₃)(Q₄₁₄)—*′, or*—C(Q₄₁₃)═C(Q₄₁₄)—*′ (wherein Q₄₁₃ and Q₄₁₄ may each independently behydrogen, deuterium, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, or a naphthyl group),but are not limited thereto.

L₄₀₂ in Formula 401 may be a monovalent, divalent, or trivalent organicligand. For example, L₄₀₂ may be selected from halogen, diketone (forexample, acetylacetonate), carboxylic acid (for example, picolinate),—C(═O), isonitrile, —CN, and phosphorus (for example, phosphine, orphosphite), but embodiments of the present disclosure are not limitedthereto.

In one or more embodiments, the phosphorescent dopant may be selectedfrom, for example, Compounds PD1 to PD25, but embodiments of the presentdisclosure are not limited thereto:

Fluorescent Dopant in Emission Layer

The fluorescent dopant may include a compound represented by Formula 1.

In addition, the fluorescent dopant may include an arylamine compound ora styrylamine compound.

In addition, the fluorescent dopant may include a compound representedby Formula 501 below:

In Formula 501,

Ar₅₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

L₅₀₁ to L₅₀₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xd1 to xd3 may each independently be an integer from 0 to 3,

R₅₀₁ and R₅₀₂ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,and

xd4 may be an integer from 1 to 6.

In one embodiment, Ar₅₀₁ in Formula 501 may be selected from:

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup; and

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, L₅₀₁ to L₅₀₃ in Formula 501 may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group.

In one or more embodiments, R₅₀₁ and R₅₀₂ in Formula 501 may eachindependently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xd4 in Formula 501 may be 2, but embodimentsof the present disclosure are not limited thereto.

For example, the fluorescent dopant may be selected from Compounds FD1to FD22:

In one or more embodiments, the fluorescent dopant may be selected fromthe following compounds, but embodiments of the present disclosure arenot limited thereto:

Electron Transport Region in Organic Layer 150

The electron transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron transport region may include at least one selected from abuffer layer, a hole blocking layer, an electron control layer, anelectron transport layer, and an electron injection layer, butembodiments of the present disclosure are not limited thereto.

For example, the electron transport region may have an electrontransport layer/electron injection layer structure, a hole blockinglayer/electron transport layer/electron injection layer structure, anelectron control layer/electron transport layer/electron injection layerstructure, or a buffer layer/electron transport layer/electron injectionlayer structure, wherein for each structure, constituting layers aresequentially stacked from an emission layer. However, embodiments of thestructure of the electron transport region are not limited thereto.

The electron transport region (for example, a buffer layer, a holeblocking layer, an electron control layer, or an electron transportlayer in the electron transport region) may include a metal-freecompound containing at least one π electron-depleted nitrogen-containingring.

The term “π electron-depleted nitrogen-containing ring,” as used herein,refers to a C₁-C₆₀ heterocyclic group having at least one *—N═*′ moietyas a ring-forming moiety.

For example, the “π electron-depleted nitrogen-containing ring” may bei) a 5-membered to 7-membered heteromonocyclic group having at least one*—N═*′ moiety, ii) a heteropolycyclic group in which two or more5-membered to 7-membered heteromonocyclic groups each having at leastone *—N═*′ moiety are condensed with each other, or iii) aheteropolycyclic group in which at least one of 5-membered to 7-memberedheteromonocyclic groups, each having at least one *—N═*′ moiety, iscondensed with at least one C₅-C₆₀ carbocyclic group.

Examples of the π electron-depleted nitrogen-containing ring include animidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, anisoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, anindazole, a purine, a quinoline, an isoquinoline, a benzoquinoline, aphthalazine, a naphthyridine, a quinoxaline, a quinazoline, a cinnoline,a phenanthridine, an acridine, a phenanthroline, a phenazine, abenzimidazole, an isobenzothiazole, a benzoxazole, an isobenzoxazole, atriazole, a tetrazole, an oxadiazole, a triazine, a thiadiazole, animidazopyridine, an imidazopyrimidine, and an azacarbazole, but are notlimited thereto.

For example, the electron transport region may include a compoundrepresented by Formula 601:

[Ar₆₀₁]_(xe11)−[(L₆₀₁)_(xe1)−R₆₀₁]_(xe21).   Formula 601

In Formula 601,

Ar₆₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xe1 may be an integer from 0 to 5,

R₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁),—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁ to Q₆₀₃ may each independently be a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or anaphthyl group, and

xe21 may be an integer from 1 to 5.

In one embodiment, at least one of Ar₆₀₁(s) in the number of xe11 andR₆₀₁(s) in the number of xe21 may include the π electron-depletednitrogen-containing ring.

In one embodiment, Ar₆₀₁ in Formula 601 may be selected from:

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In Formula 601, when xe11 is two or more, two or more Ar₆₀₁(s) may belinked via a single bond.

In one or more embodiments, Ar₆₀₁ in Formula 601 may be an anthracenegroup.

In one or more embodiments, the compound represented by Formula 601 maybe represented by Formula 601-1:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), and X₆₁₆ may be N orC(R₆₁₆), wherein at least one selected from X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ may each independently be the same as defined in connectionwith L₆₀₁,

xe611 to xe613 may each independently be the same as defined inconnection with xe1,

R₆₁₁ to R₆₁₃ may each independently be the same as defined in connectionwith R₆₀₁, and

R₆₁₄ to R₆₁₆ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In one embodiment, L₆₀₁ and L₆₁₁ to L₆₁₃ in Formulae 601 and 601-1 mayeach independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, and an azacarbazolyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and601-1 may each independently be 0, 1, or 2.

In one or more embodiments, R₆₀₁ and R₆₁₁ to R₆₁₃ in Formulae 601 and601-1 may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

—S(═O)₂(Q₆₀₁) and —P(═O)(Q₆₀₁)(Q₆₀₂), and

Q₆₀₁ and Q₆₀₂ are the same as described above.

The electron transport region may include at least one compound selectedfrom Compounds ET1 to ET36, but embodiments of the present disclosureare not limited thereto:

In one or more embodiments, the electron transport region may include atleast one compound selected from2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq,3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), and NTAZ:

Thicknesses of the buffer layer, the hole blocking layer, and theelectron control layer may each be in a range of about 20 Å to about1,000 Å, for example, about 30 Å to about 300 Å. When the thicknesses ofthe buffer layer, the hole blocking layer, and the electron controllayer are within these ranges, the hole blocking layer may haveexcellent hole blocking characteristics, and the electron control layermay have excellent electron control characteristics without asubstantial increase in driving voltage.

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within the rangedescribed above, the electron transport layer may have suitable orsatisfactory electron transport characteristics without a substantialincrease in driving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include at least one selected fromalkali metal complex and alkaline earth-metal complex. The alkali metalcomplex may include a metal ion selected from a Li ion, a Na ion, a Kion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex mayinclude a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Srion, and a Ba ion. A ligand coordinated with the metal ion of the alkalimetal complex or the alkaline earth-metal complex may be selected from ahydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, ahydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, ahydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxydiphenylthiadiazole, a hydroxy phenylpyridine, a hydroxyphenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, aphenanthroline, and a cyclopentadiene, but embodiments of the presentdisclosure are not limited thereto.

For example, the metal-containing material may include a Li complex. TheLi complex may include, for example, Compound ET-D1 (lithium quinolate,LiQ) or ET-D2:

The electron transport region may include an electron injection layerthat facilitates electron injection from the second electrode 190. Theelectron injection layer may directly contact the second electrode 190.

The electron injection layer may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In oneembodiment, the alkali metal may be Li, Na, or Cs. In one or moreembodiments, the alkali metal may be Li or Cs, but embodiments of thepresent disclosure are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkali metal compound, the alkaline earth-metal compound, and therare earth metal compound may be selected from oxides and halides (forexample, fluorides, chlorides, bromides, or iodides) of the alkalimetal, the alkaline earth-metal, and the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides, suchas Li₂O, Cs₂O, or K₂O, and alkali metal halides, such as LiF, NaF, CsF,KF, LiI, NaI, CsI, or KI. In one embodiment, the alkali metal compoundmay be selected from LiF, Li₂O, NaF, LiI, NaI, CsI, and KI, butembodiments of the present disclosure are not limited thereto.

The alkaline earth-metal compound may be selected from alkalineearth-metal oxides, such as BaO, SrO, CaO, Ba_(x)Sr_(1-x)O (0<x<1), orBa_(x)Ca_(1-x)O (0<x<1). In one embodiment, the alkaline earth-metalcompound may be selected from BaO, SrO, and CaO, but embodiments of thepresent disclosure are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, Sc₂O₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In one embodiment, the rare earth metalcompound may be selected from YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, and TbI₃,but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and the rareearth metal complex may include an ion of alkali metal, alkalineearth-metal, and rare earth metal as described above, and a ligandcoordinated with a metal ion of the alkali metal complex, the alkalineearth-metal complex, or the rare earth metal complex may be selectedfrom hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline,hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxyphenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole,hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene,but embodiments of the present disclosure are not limited thereto.

The electron injection layer may consist of an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof, as described above. In one or moreembodiments, the electron injection layer may further include an organicmaterial. When the electron injection layer further includes an organicmaterial, an alkali metal, an alkaline earth metal, a rare earth metal,an alkali metal compound, an alkaline earth-metal compound, a rare earthmetal compound, an alkali metal complex, an alkaline earth-metalcomplex, a rare earth metal complex, or any combinations thereof may behomogeneously or non-homogeneously dispersed in a matrix including theorganic material.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within the range describedabove, the electron injection layer may have suitable or satisfactoryelectron injection characteristics without a substantial increase indriving voltage.

Second Electrode 190

The second electrode 190 may be on the organic layer 150 having such astructure. The second electrode 190 may be a cathode which is anelectron injection electrode, and in this regard, a material for formingthe second electrode 190 may be selected from metal, an alloy, anelectrically conductive compound, and a combination thereof, which havea relatively low work function.

The second electrode 190 may include at least one selected from lithium(Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are notlimited thereto. The second electrode 190 may be a transmissiveelectrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layered structure, or amulti-layered structure including two or more layers.

Description of FIGS. 2 to 4

FIG. 2 is a schematic view of an organic light-emitting device 20according to an embodiment. The organic light-emitting device 20includes a first capping layer 210, the first electrode 110, the organiclayer 150, and the second electrode 190, which are sequentially stackedin this stated order. FIG. 3 is a schematic view of an organiclight-emitting device 30 according to an embodiment. The organiclight-emitting device 30 includes the first electrode 110, the organiclayer 150, the second electrode 190, and a second capping layer 220,which are sequentially stacked in this stated order. FIG. 4 is aschematic view of an organic light-emitting device 40 according to anembodiment. The organic light-emitting device 40 includes the firstcapping layer 210, the first electrode 110, the organic layer 150, thesecond electrode 190, and the second capping layer 220, which aresequentially stacked in this stated order.

Regarding FIGS. 2 to 4, the first electrode 110, the organic layer 150,and the second electrode 190 may be understood by referring to thedescription presented in connection with FIG. 1.

In the organic layer 150 of each of the organic light-emitting devices20 and 40, light generated in an emission layer may pass through thefirst electrode 110 and the first capping layer 210 toward the outside,wherein the first electrode 110 may be a semi-transmissive electrode ora transmissive electrode. In the organic layer 150 of each of theorganic light-emitting devices 30 and 40, light generated in an emissionlayer may pass through the second electrode 190 and the second cappinglayer 220 toward the outside, wherein the second electrode 190 may be asemi-transmissive electrode or a transmissive electrode.

The first capping layer 210 and the second capping layer 220 mayincrease external luminescent efficiency according to the principle ofconstructive interference.

The first capping layer 210 and the second capping layer 220 may eachindependently be an organic capping layer including an organic material,an inorganic capping layer including an inorganic material, or acomposite capping layer including an organic material and an inorganicmaterial.

At least one selected from the first capping layer 210 and the secondcapping layer 220 may each independently include at least one materialselected from carbocyclic compounds, heterocyclic compounds, amine-basedcompounds, porphyrine derivatives, phthalocyanine derivatives, anaphthalocyanine derivatives, alkali metal complexes, and alkalineearth-metal complexes. The carbocyclic compound, the heterocycliccompound, and the amine-based compound may be optionally substitutedwith a substituent containing at least one element selected from O, N,S, Se, Si, F, CI, Br, and I. In one embodiment, at least one selectedfrom the first capping layer 210 and the second capping layer 220 mayeach independently include an amine-based compound.

In one embodiment, at least one selected from the first capping layer210 and the second capping layer 220 may each independently include thecompound represented by Formula 201 or the compound represented byFormula 202.

In one or more embodiments, at least one selected from the first cappinglayer 210 and the second capping layer 220 may each independentlyinclude a compound selected from Compounds HT28 to HT33 and CompoundsCP1 to CP5, but embodiments of the present disclosure are not limitedthereto:

Hereinbefore, the organic light-emitting device according to anembodiment has been described in connection with FIGS. 1 to 4, butembodiments of the present disclosure are not limited thereto.

Layers constituting the hole transport region, an emission layer, andlayers constituting the electron transport region may be formed in acertain region by using one or more suitable methods selected fromvacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, ink-jet printing, laser-printing, and laser-induced thermalimaging.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed byvacuum deposition, the deposition may be performed at a depositiontemperature of about 100° C. to about 500° C., a vacuum degree of about10⁻⁸ torr to about 10⁻³ torr, and a deposition speed of about 0.01 Å/secto about 100 Å/sec by taking into account a material to be included in alayer to be formed, and the structure of a layer to be formed.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed by spincoating, the spin coating may be performed at a coating speed of about2,000 rpm to about 5,000 rpm and at a heat treatment temperature ofabout 80° C. to about 200° C. by taking into account a material to beincluded in a layer to be formed, and the structure of a layer to beformed.

General Definition of at Least Some of the Substituents

The term “C₁-C₆₀ alkyl group,” as used herein, refers to a linear orbranched aliphatic saturated hydrocarbon monovalent group having 1 to 60carbon atoms, and examples thereof include a methyl group, an ethylgroup, a propyl group, an isobutyl group, a sec-butyl group, atert-butyl group, a pentyl group, an isoamyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group,” as used herein, refers to a divalentgroup having substantially the same structure as the C₁-C₆₀ alkyl group.

The term “C₂-C₆₀ alkenyl group,” as used herein, refers to a hydrocarbongroup having at least one carbon-carbon double bond at a main chain(e.g., in the middle) or at a terminal end (e.g., at the terminus) ofthe C₂-C₆₀ alkyl group, and examples thereof include an ethenyl group, apropenyl group, and a butenyl group.

The term “C₂-C₆₀ alkenylene group,” as used herein, refers to a divalentgroup having substantially the same structure as the C₂-C₆₀ alkenylgroup.

The term “C₂-C₆₀ alkynyl group,” as used herein, refers to a hydrocarbongroup having at least one carbon-carbon triple bond at a main chain(e.g., in the middle) or at a terminal end (e.g., at the terminus) ofthe C₂-C₆₀ alkyl group, and examples thereof include an ethynyl group,and a propynyl group. The term “C₂-C₆₀ alkynylene group,” as usedherein, refers to a divalent group having substantially the samestructure as the C₂-C₆₀ alkynyl group.

The term “C₁-C₆₀ alkoxy group,” as used herein, refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and examples thereof include a methoxy group, an ethoxy group, and anisopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group,” as used herein, refers to amonovalent saturated hydrocarbon monocyclic group having 3 to 10 carbonatoms, and examples thereof include a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.The term “C₃-C₁₀ cycloalkylene group,” as used herein, refers to adivalent group having substantially the same structure as the C₃-C₁₀cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group,” as used herein, refers to amonovalent monocyclic group having at least one heteroatom selected fromN, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, andexamples thereof include a 1,2,3,4-oxatriazolidinyl group, atetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term“C₁-C₁₀ heterocycloalkylene group,” as used herein, refers to a divalentgroup having substantially the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group,” as used herein, refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone carbon-carbon double bond in the ring thereof and no aromaticity(e.g., the ring and/or group is not aromatic), and examples thereofinclude a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenylgroup. The term “C₃-C₁₀ cycloalkenylene group,” as used herein, refersto a divalent group having substantially the same structure as theC₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group,” as used herein, refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one carbon-carbon double bond in its ring. Non-limitingexamples of the C₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolylgroup, a 2,3-dihydrofuranyl group, and a2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup,” as used herein, refers to a divalent group having substantiallythe same structure as the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group,” as used herein, refers to a monovalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms,and a C₆-C₆₀ arylene group used herein refers to a divalent group havinga carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limitingexamples of the C₆-C₆₀ aryl group include a phenyl group, a naphthylgroup, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, anda chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylenegroup each include two or more rings, the rings may be fused to eachother (e.g., combined together).

The term “C₁-C₆₀ heteroaryl group,” as used herein, refers to amonovalent group having a carbocyclic aromatic system that has at leastone heteroatom selected from N, O, Si, P, and S as a ring-forming atom,in addition to 1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylenegroup,” as used herein, refers to a divalent group having a carbocyclicaromatic system that has at least one heteroatom selected from N, O, Si,P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms.Non-limiting examples of the C₁-C₆₀ heteroaryl group include a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, and an isoquinolinyl group. Whenthe C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylene group eachinclude two or more rings, the rings may be condensed with each other(e.g., combined together).

The term “C₆-C₆₀ aryloxy group,” as used herein, indicates —OA102(wherein A₁₀₂ is the C₆-C₆₀ aryl group), and the term “C₆-C₆₀ arylthiogroup,” as used herein, indicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀aryl group).

The term “C₁-C₆₀ heteroaryloxy group,” as used herein, refers to —OA₁₀₄(wherein A₁₀₄ is the C₁-C₆₀ heteroaryl group), and the term “C₁-C₆₀heteroarylthio group” used herein indicates —SA₁₀₅ (wherein A₁₀₅ is theC₁-C₆₀ heteroaryl group).

The term “monovalent non-aromatic condensed polycyclic group,” as usedherein, refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed with each other (e.g.,combined together), only carbon atoms as ring-forming atoms, and noaromaticity in its entire molecular structure (e.g., the entiremolecular structure is not aromatic). An example of the monovalentnon-aromatic condensed polycyclic group is a fluorenyl group. The term“divalent non-aromatic condensed polycyclic group,” as used herein,refers to a divalent group having substantially the same structure asthe monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group,” asused herein, refers to a monovalent group (for example, having 1 to 60carbon atoms) having two or more rings condensed to each other (e.g.,combined together), at least one heteroatom selected from N, O, Si, P,and S, other than carbon atoms, as a ring-forming atom, and noaromaticity in its entire molecular structure (e.g., the entiremolecular structure is not aromatic). An example of the monovalentnon-aromatic condensed heteropolycyclic group is a carbazolyl group. Theterm “divalent non-aromatic condensed heteropolycyclic group,” as usedherein, refers to a divalent group having substantially the samestructure as the monovalent non-aromatic condensed heteropolycyclicgroup.

The term “C₅-C₆₀ carbocyclic group,” as used herein, refers to amonocyclic or polycyclic group having 5 to 60 carbon atoms in which aring-forming atom is a carbon atom only. The term “C₅-C₆₀ carbocyclicgroup,” as used herein, refers to an aromatic carbocyclic group or anon-aromatic carbocyclic group. The C₅-C₆₀ carbocyclic group may be aring, such as benzene, a monovalent group, such as a phenyl group, or adivalent group, such as a phenylene group. In one or more embodiments,depending on the number of substituents connected to the C₅-C₆₀carbocyclic group, the C₅-C₆₀ carbocyclic group may be a trivalent groupor a quadrivalent group.

The term “C₁-C₆₀ heterocyclic group,” as used herein, refers to a grouphaving substantially the same structure as the C₅-C₆₀ carbocyclic group,except that as a ring-forming atom, at least one heteroatom selectedfrom N, O, Si, P, and S is used in addition to carbon (the number ofcarbon atoms may be in a range of 1 to 60).

In the present specification, at least one substituent of thesubstituted C₅-C₆₀ carbocyclic group, the substituted C₁-C₆₀heterocyclic group, the substituted C₁-C₂₀ alkylene group, theunsubstituted C₂-C₂₀ alkenylene group, the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₁₀ heterocycloalkylene group,the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, the substituted divalentnon-aromatic condensed polycyclic group, the substituted divalentnon-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedC₁-C₆₀ heteroaryloxy group, the substituted C₁-C₆₀ heteroarylthio group,the substituted monovalent non-aromatic condensed polycyclic group, andthe substituted monovalent non-aromatic condensed heteropolycyclic groupmay be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

The term “Ph,” as used herein, represents a phenyl group, the term “Me”as used herein represents a methyl group, the term “Et,” as used herein,represents an ethyl group, the term “ter-Bu” or “But,” as used herein,represents a tert-butyl group, and the term “OMe,” as used herein,represents a methoxy group.

The term “biphenyl group,” as used herein, refers to a “phenyl groupsubstituted with a phenyl group. The “biphenyl group” is a “substitutedphenyl group” having a “C₆-C₆₀ aryl group” as a substituent.

The term “terphenyl group,” as used herein, refers to a “phenyl groupsubstituted with a biphenyl group. The “terphenyl group” is a“substituted phenyl group” having, as a substituent, a “C₆-C₆₀ arylgroup substituted with a C₆-C₆₀ aryl group”.

* and *′ used herein, unless defined otherwise, each refer to a bindingsite to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and an organiclight-emitting device according to embodiments will be described in moredetail with reference to Synthesis Examples and Examples. The expression“B was used instead of A” used in describing Synthesis Examples meansthat an identical number of molar equivalents of B was used in place ofmolar equivalents of A.

EXAMPLE Synthesis Example Synthesis Example 1: Synthesis of Compound 5

Intermediate 5-1(4-bromo-10-(2-bromo-4-(tert-butyl)phenyl)-2-(tert-butyl)-9,9-dimethyl-9,10-dihydroacridine)(1 eq) was dissolved in tetrahydrofuran (THF) and cooled to atemperature of −78° C., and n-BuLi (2.2 eq) was slowly added thereto.After the reaction solution was stirred for 2 hours at a lowtemperature, a solution in which dimethyl phenylboronate (2.0 eq) wasdiluted in THF was added to a reaction container. The reaction solutionwas further stirred at a temperature of −78° C. for 1 hour and stirredat room temperature for 2 hours. The reaction solution was stirred at atemperature of 80° C. for 24 hours under reflux and was added to NH₄Claqueous solution to terminate the reaction. An organic layer wasextracted therefrom three times by using distilled water and ethylacetate (EA), dried by using MgSO₄, and then dried under reducedpressure. The obtained organic layer was purified by columnchromatography (MC/Hex) to obtain Compound 5 (yield: 35%).

Synthesis Example 2: Synthesis of Compound 52

Compound 52 (yield: 21%) was synthesized in substantially the samemanner as in Synthesis Example 1, except that Intermediate 52-1(4-bromo-10-(2-bromo-5-(9H-carbazol-9-yl)phenyl)-9,9-diphenyl-9,10-dihydroacridine)was used instead of Intermediate 5-1.

Synthesis Example 3: Synthesis of Compound 71

Compound 71 (yield: 33%) was synthesized in substantially the samemanner as in Synthesis Example 1, except that Intermediate 71-1(5-bromo-10-(2-bromophenyl)-2-(9H-carbazol-9-yl)-10H-spiro[acridine-9,9′-fluorene])was used instead of Intermediate 5-1.

Synthesis Example 4: Synthesis of Compound 82

Compound 82 (yield: 31%) was synthesized in substantially the samemanner as in Synthesis Example 1, except that Intermediate 82-1(4-bromo-5-(2-bromo-5-(9H-carbazol-9-yl)phenyl)-10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasiline)was used instead of Intermediate 5-1.

Synthesis Example 5: Synthesis of Compound 139

Compound 139 (yield: 26%) was synthesized in substantially the samemanner as in Synthesis Example 1, except that Intermediate 139-1(4-bromo-10-(2-bromophenyl)-10′-phenyl-10H,10′H-9,9′-spirobi[acridine])was used instead of Intermediate 5-1.

Synthesis Example 6: Synthesis of Compound 145

Compound 145 (yield: 39%) was synthesized in substantially the samemanner as in Synthesis Example 1, except that Intermediate 145-1(4-bromo-10-(2-bromophenyl)-10H-spiro[acridine-9,9′-xanthene]) was usedinstead of Intermediate 5-1.

Synthesis Example 7: Synthesis of Compound 147

Compound 147 (yield: 21%) was synthesized in substantially the samemanner as in Synthesis Example 1, except that Intermediate 147-1(4-bromo-10-(2-bromophenyl)-10H-spiro[acridine-9,9′-thioxanthene]) wasused instead of Intermediate 5-1.

Synthesis Example 8: Synthesis of Compound 156

Compound 156 (yield: 19%) was synthesized in substantially the samemanner as in Synthesis Example 1, except that Intermediate 156-1(10,10′-(4,6-dibromo-1,3-phenylene)bis(4-bromo-9,9-diphenyl-9,10-dihydroacridine))was used instead of Intermediate 5-1.

¹H NMR and MS/FAB of Compounds synthesized according to SynthesisExamples 1 to 8 are shown in Table 1.

Synthesis methods of compounds other than Compounds shown in Table 1 mayalso be easily recognized by those of ordinary skill in the art byreferring to the synthesis mechanisms and starting materials describedherein above.

TABLE 1 MS/FAB Compound ¹H NMR (CDCI₃, 400 MHz) found calc. 5 7.85-7.79(2H, m), 7.45-7.30 483.50 483.51 (4H, m), 7.28-7.25 (1H, m), 7.19-7.02(4H, m), 6.99-6.85 (2H, m), 6.87-7.82 (1H, m), 1.65-1.57 (6H, m),1.41-1.32 (18H, m) 52 8.61-8.55 (1H, m), 8.21-8.15 660.62 660.63 (1H,m), 7.88-7.85 (1H, m), 7.79-7.72 (2H, m), 7.62-7.51 (2H, m), 7.35-7.12(24H, m), 6.89-6.98 (2H, m) 71 8.60-8.54 (1H, m), 8.20-8.15 658.60658.61 (1H, m), 7.98-7.89 (2H, m), 7.79-7.70 (4H, m), 7.686-7.51 (5H,m), 7.41-6.98 (18H, m), 82 8.58-8.54 (1H, m), 8.18-8.15 676.69 676.7(1H, m), 7.88-7.69 (4H, m), 7.52-7.38 (19H, m), 7.31-7.05 (8H, m) 1397.78-7.74 (3H, m), 7.68-8.65 584.52 584.53 (1H, m), 7.48-7.19 (6H, m),7.22-6.88 (19H, m) 145 7.86-7.74 (3H, m), 7.65-7.60 509.41 509.42 (1H,m), 7.49-6.78 (20H, m) 147 7.76-7.65 (5H, m), 7.62-7.60 525.47 525.48(1H, m), 7.42-7.16 (6H, m), 7.22-6.96 (12H, m) 156 7.80-7.71 (4H, m),7.72-7.65 912.74 912.75 (2H, m), 7.39-7.03 (35H, m), 6.99-6.91 (2H, m),6.90-6.81 (3H, m)

Example 1

As an anode, a Corning 15 Ω/cm² (1,200 Å) ITO glass substrate was cut toa size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and purewater each for 5 minutes, and then cleaned by exposure to ultravioletrays and ozone for 30 minutes. Then, the ITO glass substrate wasprovided to a vacuum deposition apparatus.

An existing compound NPD was vacuum-deposited on the ITO glass substrateto form a hole injection layer having a thickness of 300 Å, and a holetransport compound TCTA was vacuum-deposited on the hole injection layerto form a hole transport layer having a thickness of 200 Å.

A hole transport compound CzSi was vacuum-deposited on the holetransport layer to form a layer having a thickness of 100 Å. DPEPO andCompound 5 were co-deposited on the layer to a weight ratio of 90:10 toform an emission layer having a thickness of 200 Å.

Then, an electron transport compound DPEPO was formed to a thickness of200 Å, and an electron injection compound TPBI was formed to a thicknessof 300 Å.

LiF, which is alkali metal halide, was deposited on the electrontransport layer to form an electron injection layer having a thicknessof 10 Å, and Al was vacuum-deposited to a thickness of 3,000 Å (cathodeelectrode) to form an LiF/Al electrode, thereby completing themanufacture of an organic light-emitting device.

Examples 2 to 8 and Comparative Examples 1 to 3

Organic light-emitting devices were manufactured in substantially thesame manner as in Example 1, except that Compounds shown in Table 2 wereeach used instead of Compound 5 in forming an emission layer.

Evaluation Example

The driving voltage, efficiency, and color purity of the organiclight-emitting devices manufactured according to Examples 1 to 8 andComparative Examples 1 to 3 were measured at a current density of 10mA/cm² by using the following methods, and results thereof are shown inTable 2.

Color coordinates: Power was supplied by using a current-voltage meter(Keithley SMU 236), and color coordinates were measured by using aluminance meter PR650.

Luminance: Power was supplied by using a current-voltage meter (KeithleySMU 236), and luminance was measured by using a luminance meter PR650.

Efficiency: Power was supplied by using a current-voltage meter(Keithley SMU 236), and efficiency was measured by using a luminancemeter PR650.

TABLE 2 Driving Efficiency Emission Dopant in emission layer voltage (V)(cd/A) color Example 1 Compound 5 4.50 21.5 Blue Example 2 Compound 524.72 23.9 Blue Example 3 Compound 71 4.88 25.2 Blue Example 4 Compound82 4.70 20.5 Blue Example 5 Compound 139 4.52 22.9 Blue Example 6Compound 145 4.60 21.3 Blue Example 7 Compound 147 4.85 20.0 BlueExample 8 Compound 156 4.37 21.5 Blue Comparative DPS 6.7 19.3 BlueExample 1 Comparative Compound A 6.1 11.3 Dark blue Example 2Comparative Compound B 5.9 12.5 Dark blue Example 3

Referring to Table 2, it is confirmed that the organic light-emittingdevices of Examples 1 to 8 in which the compound according to one ormore embodiments is used in the emission layer have a low drivingvoltage and improved efficiency, as compared with those of the organiclight-emitting devices of Comparative Examples 1 to 3. In addition, itis confirmed that the organic light-emitting devices in which thecompound according to one or more embodiments is used in the emissionlayer emit blue light.

In some embodiments, when the compound according to one or moreembodiments is used as a material for forming an emission layer, thedriving voltage and efficiency are excellent, and it is suitable forblue light emission.

The organic light-emitting device including the heterocyclic compoundmay have a low driving voltage, high efficiency, and a long lifespan.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould be considered as available for other similar features or aspectsin other embodiments.

It will be understood that, although the terms “first,” “second,”“third,” etc., may be used herein to describe various elements,components, regions, layers and/or sections, these elements, components,regions, layers and/or sections should not be limited by these terms.These terms are used to distinguish one element, component, region,layer or section from another element, component, region, layer orsection. Thus, a first element, component, region, layer or sectiondescribed herein could be termed a second element, component, region,layer or section, without departing from the spirit and scope of thepresent disclosure.

Spatially relative terms, such as “beneath,” “below,” “lower,” “under,”“above,” “upper,” and the like, may be used herein for ease ofexplanation to describe one element or feature's relationship to anotherelement(s) or feature(s) as illustrated in the figures. It will beunderstood that the spatially relative terms are intended to encompassdifferent orientations of the device in use or in operation, in additionto the orientation depicted in the figures. For example, if the devicein the figures is turned over, elements described as “below” or“beneath” or “under” other elements or features would then be oriented“above” the other elements or features. Thus, the example terms “below”and “under” can encompass both an orientation of above and below. Thedevice may be otherwise oriented (e.g., rotated 90 degrees or at otherorientations) and the spatially relative descriptors used herein shouldbe interpreted accordingly.

It will be understood that when an element or layer is referred to asbeing “on,” “connected to,” or “coupled to” another element or layer, itcan be directly on, connected to, or coupled to the other element orlayer, or one or more intervening elements or layers may be present. Inaddition, it will also be understood that when an element or layer isreferred to as being “between” two elements or layers, it can be theonly element or layer between the two elements or layers, or one or moreintervening elements or layers may also be present.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting of the presentdisclosure. As used herein, the singular forms “a” and “an” are intendedto include the plural forms as well, unless the context clearlyindicates otherwise. It will be further understood that the terms“comprises,” “comprising,” “includes,” and “including,” when used inthis specification, specify the presence of the stated features,integers, acts, operations, elements, and/or components, but do notpreclude the presence or addition of one or more other features,integers, acts, operations, elements, components, and/or groups thereof.

As used herein, the terms “substantially,” “about,” and similar termsare used as terms of approximation and not as terms of degree, and areintended to account for the inherent deviations in measured orcalculated values that would be recognized by those of ordinary skill inthe art. Further, the use of “may” when describing embodiments of thepresent disclosure refers to “one or more embodiments of the presentdisclosure.” As used herein, the terms “use,” “using,” and “used” may beconsidered synonymous with the terms “utilize,” “utilizing,” and“utilized,” respectively. Also, the term “exemplary” is intended torefer to an example or illustration.

Also, any numerical range recited herein is intended to include allsub-ranges of the same numerical precision subsumed within the recitedrange. For example, a range of “1.0 to 10.0” is intended to include allsubranges between (and including) the recited minimum value of 1.0 andthe recited maximum value of 10.0, that is, having a minimum value equalto or greater than 1.0 and a maximum value equal to or less than 10.0,such as, for example, 2.4 to 7.6. Any maximum numerical limitationrecited herein is intended to include all lower numerical limitationssubsumed therein, and any minimum numerical limitation recited in thisspecification is intended to include all higher numerical limitationssubsumed therein. Accordingly, Applicant reserves the right to amendthis specification, including the claim, to expressly recite anysub-range subsumed within the ranges expressly recited herein.

While one or more embodiments have been described with reference to thefigures, it will be understood by those of ordinary skill in the artthat various changes in form and details may be made therein withoutdeparting from the spirit and scope as defined by the following claim,and equivalents thereof.

What is claimed is:
 1. An organic light-emitting device comprising: afirst electrode; a second electrode facing the first electrode; and anorganic layer between the first electrode and the second electrode andcomprising an emission layer, wherein the organic layer comprises atleast one heterocyclic compound represented by Formula 1:

wherein, in Formula 1, Y₁ is N or P, Y₂ is B(R₁), P(═O)(R₁), orP(═S)(R₁), X₁ and X₂ are each independently O, S, N(R₂), C(R₂)(R₃), orSi(R₂)(R₃), m1 and m2 are each independently 0, 1, or 2, whereinm1+m2>0, A₁ to A₃ are each independently a substituted or unsubstitutedC₅-C₆₀ carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group, a10, a20, and a30 are each independently selectedfrom 0, 1, 2, 3, 4, 5, 6, 7, and 8, R₁ to R₃, R₁₀, R₂₀, and R₃₀ are eachindependently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂),—C(═O)(Q₁), —N(Q₁)(Q₂), P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁)(Q₂), R₁ to R₃,R₁₀, R₂₀, and R₃₀ are optionally linked to form a substituted orunsubstituted C₅-C₆₀ carbocyclic group or a substituted or unsubstitutedC₁-C₆₀ heterocyclic group, at least one substituent of the substitutedC₅-C₆₀ carbocyclic group, the substituted C₁-C₆₀ heterocyclic group, thesubstituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenyl group,the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxygroup, the substituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group is selectedfrom: deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂),—B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group; a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂),—B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ toQ₂₃, and Q₃₁ to Q₃₃ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, a monovalent non-aromatic condensedheteropolycyclic group, a biphenyl group, and a terphenyl group.
 2. Theorganic light-emitting device of claim 1, wherein: the first electrodeis an anode, the second electrode is a cathode, the organic layerfurther comprises a hole transport region between the first electrodeand the emission layer and an electron transport region between theemission layer and the second electrode, the hole transport regioncomprises a hole injection layer, a hole transport layer, an emissionauxiliary layer, an electron blocking layer, or any combination thereof,and the electron transport region comprises a hole blocking layer, anelectron transport layer, an electron injection layer, or anycombination thereof.
 3. The organic light-emitting device of claim 1,wherein: the emission layer comprises the at least one of theheterocyclic compound represented by Formula
 1. 4. The organiclight-emitting device of claim 3, wherein: the emission layer consistsof the at least one of the heterocyclic compound represented by Formula1; or the emission layer further comprises a host, and an amount of theat least one of the heterocyclic compound represented by Formula 1 is ina range about 0.1 parts by weight to about 50 parts by weight based on100 parts by weight of the emission layer.
 5. The organic light-emittingdevice of claim 3, wherein: the at least one of the heterocycliccompound represented by Formula 1 comprised in the emission layer is athermally activated delayed fluorescence (TADF) emitter, and theemission layer emits delayed fluorescence.
 6. The organic light-emittingdevice of claim 3, wherein: the emission layer does not comprise anorganometallic compound.
 7. The organic light-emitting device of claim3, wherein: the emission layer is configured to emit blue light having amaximum emission wavelength of 430 nm or more and 480 nm or less.
 8. Theorganic light-emitting device of claim 2, wherein: the hole transportregion comprises a p-dopant, and the p-dopant has a lowest unoccupiedmolecular orbital (LUMO) energy level of −3.5 eV or less.
 9. Aheterocyclic compound represented by Formula 1:

wherein, in Formula 1, Y₁ is N or P, Y₂ is B(R₁), P(═O)(R₁), orP(═S)(R₁), X₁ and X₂ are each independently O, S, N(R₂), C(R₂)(R₃), orSi(R₂)(R₃), m1 and m2 are each independently 0, 1, or 2, whereinm1+m2>0, A₁ to A₃ are each independently a substituted or unsubstitutedC₅-C₆₀ carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group, a10, a20, and a30 are each independently selectedfrom 0, 1, 2, 3, 4, 5, 6, 7, and 8, R₁ to R₃, R₁₀, R₂₀, and R₃₀ are eachindependently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂),—C(═O)(Q₁), —N(Q₁)(Q₂), —P(═O)(Q₁)(Q₂), and —S(═O)₂(Q₁)(Q₂), R₁ to R₃,R₁₀, R₂₀, and R₃₀ are optionally linked to form a substituted orunsubstituted C₅-C₆₀ carbocyclic group or a substituted or unsubstitutedC₁-C₆₀ heterocyclic group, at least one substituent of the substitutedC₅-C₆o carbocyclic group, the substituted C₁-C₆₀ heterocyclic group, thesubstituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenyl group,the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxygroup, the substituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group is selectedfrom: deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂),—B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group; a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂),—B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ toQ₂₃, and Q₃₁ to Q₃₃ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, a monovalent non-aromatic condensedheteropolycyclic group, a biphenyl group, and a terphenyl group.
 10. Theheterocyclic compound of claim 9, wherein: m1 is 1, and m2 is 0 or 1.11. The heterocyclic compound of claim 9, wherein: A₁ and A₂ are eachindependently selected from a benzene group, a naphthalene group, aphenanthrene group, an anthracene group, a triphenylene group, a pyrenegroup, a chrysene group, a pyridine group, a pyrazine group, apyrimidine group, a triazine group, a quinoline group, an isoquinolinegroup, a benzoquinoline group, a benzoisoquinoline group, a2,6-naphthyridine group, a 1,8-naphthyridine group, a 1,5-naphthyridinegroup, a 1,6-naphthyridine group, a 1,7-naphthyridine group, a2,7-naphthyridine group, a quinoxaline group, a quinazoline group, aphenanthridine group, and a phenanthroline group.
 12. The heterocycliccompound of claim 9, wherein: A₃ is selected from a benzene group, anaphthalene group, a phenanthrene group, an anthracene group, atriphenylene group, a pyrene group, a chrysene group, a pyridine group,a pyrazine group, a pyrimidine group, a triazine group, a quinolinegroup, an isoquinoline group, a benzoquinoline group, abenzoisoquinoline group, a 2,6-naphthyridine group, a 1,8-naphthyridinegroup, a 1,5-naphthyridine group, a 1,6-naphthyridine group, a1,7-naphthyridine group, a 2,7-naphthyridine group, a quinoxaline group,a quinazoline group, a phenanthridine group, a phenanthroline group, abenzofuran group, a benzothiophene group, an indene group, an indolegroup, a furopyridine group, a thienopyridine group, acyclopentapyridine group, a pyrrolopyridine group, a dibenzofuran group,a dibenzothiophene group, a fluorene group, a carbazole group, abenzonaphthofuran group, a benzonaphthothiophene group, a benzofluorenegroup, a benzocarbazole group, a dinaphthofuran group, adinaphthothiophene group, a dibenzofluorene group, a dibenzocarbazolegroup, a benzoxazole group, a benzothiazole group, a benzimidazolegroup, a naphthofuran, a naphthothiophene, a spiro-bifluorene group, anda spiro-fluorene-indene group; and a group represented by Formula 1A:

wherein, in Formula 1A, Y₂₁ is N or P, Y₂₂ is B(R₄), P(═O)(R₄), orP(═S)(R₄), X₂₁ and X₂₂ are each independently O, S, N(R₅), C(R₅)(R₆), orSi(R₅)(R₆), m21 and m22 are each independently 0, 1, or 2, and satisfym21+m22>0, A₂₁ to A₂₃ are each independently a substituted orunsubstituted C₅-C₆₀ carbocyclic group or a substituted or unsubstitutedC₁-C₆₀ heterocyclic group, a40, a50, and a60 are the same as defined inconnection with a10, a20, and a30 in claim 9, R₄ is the same as definedin connection with R₁ in claim 9, R₅ and R₆ are each independently thesame as defined in connection with R₂ and R₃ in claim 9, and R₄₀, R₅₀,and R₆₀ are each independently the same as defined in connection withR₁₀, R₂₀, and R₃₀ in claim
 9. 13. The heterocyclic compound of claim 9,wherein: the heterocyclic compound represented by Formula 1 isrepresented by one selected from Formulae 2-1 to 2-3:

wherein, in Formulae 2-1 to 2-3, Y₁, Y₂, X₁, and X₂ are eachindependently the same as described in claim 9, Y₂₁ is N or P, Y₂₂ isB(R₄), P(═O)(R₄), or P(═S)(R₄), X₂₁ is O, S, N(R₅), C(R₅)(R₆), orSi(R₅)(R₆), A₁₁ to A₁₃ and A₂₁ to A23 are each independently selectedfrom a benzene group, a naphthalene group, a phenanthrene group, ananthracene group, a triphenylene group, a pyrene group, a chrysenegroup, a pyridine group, a pyrazine group, a pyrimidine group, atriazine group, a quinoline group, an isoquinoline group, abenzoquinoline group, a benzoisoquinoline group, a quinoxaline group, aquinazoline group, a phenanthridine group, a phenanthroline group, adibenzofuran group, a dibenzothiophene group, a fluorene group, acarbazole group, a benzonaphthofuran group, a benzonaphthothiophenegroup, a benzofluorene group, and a benzocarbazole group, a10, a20, a30,a40, a50, and a60 are the same as defined in connection with a10, a20,a30 in claim 9, R₁₀, R₂₀, and R₃₀ are each independently the same asdescribed in claim 9, R₄ is the same as defined in connection with R₁ inclaim 9, R₅ and R₆ are each independently the same as defined inconnection with R₂ and R₃ in claim 9, and R₄₀, R₅₀, and R₆₀ are eachindependently the same as defined in connection with R₁₀, R₂₀, and R₃₀in claim
 9. 14. The heterocyclic compound of claim 9, wherein: theheterocyclic compound represented by Formula 1 is represented by oneselected from Formulae 10-1 to 10-17:

wherein, in Formulae 10-1 to 10-17, Y₁, Y₂, X₁, and X₂ are eachindependently the same as described in claim 9, R₁₁ to R₁₅ are eachindependently the same as defined in connection with R₁₀ in claim 9, R₂₁to R₂₆ are each independently the same as defined in connection with R₂₀in claim 9, R₃₁ to R₃₆ are each independently the same as defined inconnection with R₃₀ in claim 9, Y₂₁ is N or P, Y₂₂ is B(R₄), P(═O)(R₄),or P(═S)(R₄), X₂₁ is C(R₅)(R₆) or Si(R₅)(R₆), R₄ is the same as definedin connection with R₁ in claim 9, R₅ and R₆ are each independently thesame as defined in connection with R₂ and R₃ in claim 9, R₄₁ to R₄₃ areeach independently the same as defined in connection with R₁₀ in claim9, R₅₁ to R₅₄ are each independently the same as defined in connectionwith R₂₀ in claim 9, R₆₁ and R₆₂ are each independently the same asdefined in connection with R₃₀ in claim 9, and two or more neighboringsubstituents selected from R₁₁ to R₁₅, R₂₁ to R₂₆, R₃₁ to R₃₆, R₄₁ toR₄₃, R₅₁ to R₅₄, R₆₁, and R₆₂ are optionally linked to form a benzenegroup or a naphthalene group.
 15. The heterocyclic compound of claim 9,wherein: R₁ to R₃ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₆-C₆₀aryl group, —Si(Q₁)(Q₂)(Q₃), and —N(Q₁)(Q₂), Q₁ to Q₃ are eachindependently selected from hydrogen, deuterium, a C₁-C₆₀ alkyl group, aC₁-C₆₀ alkoxy group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, a biphenyl group, and aterphenyl group, and R₂ and R₃ are linked to form a substituted orunsubstituted C₅-C₆₀ carbocyclic group or a substituted or unsubstitutedC₁-C₆₀ heterocyclic group.
 16. The heterocyclic compound of claim 9,wherein: R₁ to R₃ are each independently selected from: hydrogen,deuterium, —F, —Cl, —Br, —I, a methyl group, an ethyl group, an n-propylgroup, an isopropyl group, an n-butyl group, a sec-butyl group, anisobutyl group, a tert-butyl group, an ethenyl group, a propenyl group,a butenyl group, a methoxy group, an ethoxy group, an n-propoxy group,an isopropoxy group, an n-butoxy group, a sec-butoxy group, an isobutoxygroup, and a tert-butoxy group; a methyl group, an ethyl group, ann-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group,an isobutyl group, a tert-butyl group, a methoxy group, an ethoxy group,an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxygroup, an isobutoxy group, and a tert-butoxy group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a cyanogroup, a phenyl group, and a biphenyl group; a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, and apentacenyl group; a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, abiphenyl group, a terphenyl group, a pentalenyl group, an indenyl group,a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, and apentacenyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethylgroup, an n-propyl group, an isopropyl group, an n-butyl group, asec-butyl group, an isobutyl group, a tert-butyl group, a methoxy group,an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxygroup, a sec-butoxy group, an isobutoxy group, and a tert-butoxy group;and —N(Q₁)(Q₂), and when X₁ in Formula 1 is C(R₂)(R₃) or Si(R₂)(R₃), R₂and R₃ are optionally linked to form a group represented by one selectedfrom Formulae 9-1 and 9-2:

wherein, in Formulae 9-1 and 9-2, X₁₁ is C or Si, when X₁ in Formula 1is C(R₂)(R₃), X₁₁ is C, and when X₁ in Formula 1 is Si(R₂)(R₃), X₁₁ isSi, X₉₁ and X₉₃ are each independently selected from a single bond, O,S, Se, N(R₉₄), B(R₉₄), P(═O)(R₉₄), P(═S)(R₉₄), C(R₉₄)(R₉₅),Si(R₉₄)(R₉₅), and Ge(R₉₄)(R₉₅), X₉₂ is selected from N, B, and P, A₉₁ toA₉₃ are each independently selected from a C₅-C₃₀ carbocyclic group anda C₁-C₃₀ heterocyclic group, R₉₁ to R₉₅ are each independently selectedfrom hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substitutedor unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstitutedC₁-C₆₀ heteroarylthio group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and—P(═O)(Q₁)(Q₂), Q₁ to Q₃ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a naphthyridinyl group, a quinoxalinyl group, a quinazolinylgroup, a carbazolyl group, a phenanthridinyl group, an acridinyl group,a phenanthrolinyl group, a phenazinyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, and aterphenyl group, and b91 to b93 are each independently an integer from 1to
 10. 17. The heterocyclic compound of claim 16, wherein: A₉₁ to A₉₃are each independently selected from a benzene group, a naphthalenegroup, a phenanthrene group, an anthracene group, a pyridine group, apyrazine group, a pyrimidine group, a quinoline group, an isoquinolinegroup, a benzoquinoline group, a benzoisoquinoline group, a dibenzofurangroup, a dibenzothiophene group, a fluorene group, and a carbazolegroup.
 18. The heterocyclic compound of claim 9, wherein: R₁₀, R₂₀, andR₃₀ are each independently selected from hydrogen, deuterium, —F, —Cl,—Br, —I, a cyano group, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₆-C₆₀ aryl group, a substitutedor unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), and —N(Q₁)(Q₂), and Q₁ to Q₃ are each independentlyselected from hydrogen, deuterium, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxygroup, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, a biphenyl group, and a terphenylgroup.
 19. The heterocyclic compound of claim 9, wherein: R₁₀, R₂₀, andR₃₀ are each independently selected from: hydrogen, deuterium, —F, —Cl,—Br, —I, a methyl group, an ethyl group, an n-propyl group, an isopropylgroup, an n-butyl group, a sec-butyl group, an isobutyl group, atert-butyl group, an ethenyl group, a propenyl group, a butenyl group, amethoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group,an n-butoxy group, a sec-butoxy group, an isobutoxy group, and atert-butoxy group; and a group represented by one selected from Formulae5-1 to 5-26 and 6-1 to 6-55:

wherein, in Formulae 5-1 to 5-26 and 6-1 to 6-55, Y₃₁ and Y₃₂ is O, S,C(Z₃₄)(Z₃₅), N(Z₃₄), or Si(Z₃₄)(Z₃₅), Z₃₁, Z₃₂, Z₃₄ and Z₃₅ are eachindependently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a phenanthrenyl group, ananthracenyl group, a triphenylenyl group, a pyridinyl group, apyrimidinyl group, a carbazolyl group, and a triazinyl group, e2 is 1 or2, e3 is an integer from 1 to 3, e4 is an integer from 1 to 4, e5 is aninteger from 1 to 5, e6 is an integer from 1 to 6, e7 is an integer from1 to 7, e9 is an integer from 1 to 9, and * indicates a binding site toa neighboring atom.
 20. The heterocyclic compound of claim 9, wherein:the heterocyclic compound is selected from Compounds 1 to 165: